Literature DB >> 18072785

Biomimetic synthesis of the shimalactones.

Vladimir Sofiyev1, Gabriel Navarro, Dirk Trauner.   

Abstract

A biomimetic synthesis of shimalactone A and B is described. Its key features are an unprecedented acid-catalyzed cyclization of a dienyl beta-ketolactone and a Stille coupling/8pi-6pi electrocyclization cascade to create the oxabicyclo[2.2.1]heptane and bicyclo[4.2.0]octadiene, respectively. The synthesis is convergent and void of protecting groups.

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Year:  2007        PMID： 18072785     DOI： 10.1021/ol702806v

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  10 in total

1.  Asymmetric induction in 8π electrocyclizations. Design of a removable chiral auxiliary.

Authors:  Keunsoo Kim; Joseph W Lauher; Kathlyn A Parker
Journal:  Org Lett       Date:  2011-12-06       Impact factor: 6.005

2.  Torquoselective ring closures of chiral amido trienes derived from allenamides. A tandem allene isomerization-pericyclic ring-closure-intramolecular Diels-Alder cycloaddition.

Authors:  Ryuji Hayashi; John B Feltenberger; Richard P Hsung
Journal:  Org Lett       Date:  2010-03-19       Impact factor: 6.005

3.  Stereoselective 6π-electron electrocyclic ring closures of 2-halo-amidotrienes via a remote 1,6-asymmetric induction.

Authors:  Ryuji Hayashi; Mary C Walton; Richard P Hsung; John H Schwab; Xueliang Yu
Journal:  Org Lett       Date:  2010-11-19       Impact factor: 6.005

Review 4.  Protecting-group-free synthesis as an opportunity for invention.

Authors:  Ian S Young; Phil S Baran
Journal:  Nat Chem       Date:  2009-06       Impact factor: 24.427

5.  STILLE CROSS-COUPLING REACTIONS OF ARYL MESYLATES AND TOSYLATES USING A BIARYLPHOSPHINE BASED CATALYST SYSTEM.

Authors:  John R Naber; Brett P Fors; Xiaoxing Wu; Jonathon Gunn; Stephen L Buchwald
Journal:  Heterocycles       Date:  2010-02-26       Impact factor: 0.831

6.  Discovery and Elucidation of the Biosynthesis of Aspernidgulenes: Novel Polyenes from Aspergillus Nidulans by Using Serial Promoter Replacement.

Authors:  Tzu-Shyang Lin; Bethany Chen; Yi-Ming Chiang; Clay C C Wang
Journal:  Chembiochem       Date:  2018-12-06       Impact factor: 3.164

7.  An efficient and practical entry to 2-amido-dienes and 3-amido-trienes from allenamides through stereoselective 1,3-hydrogen shifts.

Authors:  Ryuji Hayashi; John B Feltenberger; Andrew G Lohse; Mary C Walton; Richard P Hsung
Journal:  Beilstein J Org Chem       Date:  2011-04-07       Impact factor: 2.883

8.  Bioinspired Asymmetric Total Synthesis of Emeriones A-C.

Authors:  Sven Jänner; Daniel Isak; Yuli Li; Kendall N Houk; Aubry K Miller
Journal:  Angew Chem Int Ed Engl       Date:  2022-06-28       Impact factor: 16.823

9.  Total synthesis of endiandric acid J and beilcyclone A from cyclooctatetraene.

Authors:  Oussama Yahiaoui; Adrian Almass; Thomas Fallon
Journal:  Chem Sci       Date:  2020-07-29       Impact factor: 9.825

10.  Recoverable Palladium-Catalyzed Carbon-Carbon Bond Forming Reactions under Thermomorphic Mode: Stille and Suzuki-Miyaura Reactions.

Authors:  Eskedar Tessema; Vijayanath Elakkat; Chiao-Fan Chiu; Zong-Lin Tsai; Ka Long Chan; Chia-Rui Shen; Han-Chang Su; Norman Lu
Journal:  Molecules       Date:  2021-03-05       Impact factor: 4.411
  10 in total

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